Trimethyl phosphite → HCID 23208053, compound

HRID 233440Notes

Reaction equation

HRID 233440 reaction equation
[F:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6]Br)=[CH:4][CH:3]=1.[CH3:10][O:11][P:12]([O:15]C)[O:13][CH3:14]>>[F:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][P:12](=[O:15])([O:13][CH3:14])[O:11][CH3:10])=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 8472Trimethyl phosphiteHCID 680214-Fluorobenzyl bromide

Product 1

HCID 23208053HCID 23208053, compound

Procedure

A mixture of 4-fluorobenzyl bromide (4.86 g, 0.026M) and trimethylphosphite (10 mL, 0.085M) is heated at the reflux temperature for 48 hours. The solution is cooled and excess trimethylphosphite is removed under reduced pressure. The crude product is chromatographed over silica gel (40-63 mμ, 400 g, 45 mL fractions, ethyl acetate), eluting with ethyl acetate. Fractions 41-80 are combined, concentrated, and placed under vacuum for 36 hours. The product (4.52 g) is a colorless oil.

Workup

  1. temperatureis heated at the reflux temperature for 48 hours
  2. temperatureThe solution is cooled
  3. customexcess trimethylphosphite is removed under reduced pressure
  4. customThe crude product is chromatographed over silica gel (40-63 mμ, 400 g, 45 mL fractions, ethyl acetate)
  5. washeluting with ethyl acetate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-55882e58f9774087b41d1694d6d8bf38
Source dataset
uspto-grants-1997_01
Patent number
US05593980

Reaction notes

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